Dimethylformamide → (S)-Ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(4'-fluoro-2'-hydroxy-[1,1'-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

Participants

Reaction Conditions

Reaction Steps

To (S)-ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.38 g, 0.63 mmol, 1 equiv), (4-fluoro-2-hydroxyphenyl)boronic acid (148 mg, 0.95 mmol, 1.5 equiv), and Pd(PPh3)4 (73 mg, 0.063 mmol, 0.1 equiv) was added DMF (6.3 mL that had been degassed by sparging with nitrogen for 10 min) Na2CO3 (0.63 mL of a 2 M aqueous solution, 1.27 mmol, 2 equiv) was added and the reaction was heated to 90° C. for 18 h. Upon cooling to ambient temperature, the reaction was diluted with EtOAc and washed with water. The EtOAc layer was dried (Na2SO4) and concentrated in vacuo. The crude product was purified by flash column chromatography (0-100% EtOAc in hexane) to provide the product as a yellow glass (0.27 g, 68%). LCMS (M+1)=631.4.

Provenance & Evidence